(1R,2R,4S,5R,6S,13R)-4,5,13-trihydroxy-2,6,13-trimethyl-8-oxatricyclo[4.4.3.01,5]tridecane-9,12-dione

Details

• Internal ID: cc99e22e-2c19-4a22-a16e-8fa21b8208be
• Taxonomy: Organoheterocyclic compounds > Lactones
• IUPAC Name: (1R,2R,4S,5R,6S,13R)-4,5,13-trihydroxy-2,6,13-trimethyl-8-oxatricyclo[4.4.3.01,5]tridecane-9,12-dione
• SMILES (Canonical): CC1CC(C2(C13CC(=O)C(C2(COC(=O)C3)C)(C)O)O)O
• SMILES (Isomeric): C[C@@H]1C[C@@H]([C@]2([C@@]13CC(=O)[C@]([C@]2(COC(=O)C3)C)(C)O)O)O
• InChI: InChI=1S/C15H22O6/c1-8-4-9(16)15(20)12(2)7-21-11(18)6-14(8,15)5-10(17)13(12,3)19/h8-9,16,19-20H,4-7H2,1-3H3/t8-,9+,12-,13+,14-,15+/m1/s1
• InChI Key: NOHXYGXFTACADH-FKCIBCMVSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₆
• Molecular Weight: 298.33 g/mol
• Exact Mass: 298.14163842 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -0.22
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8268	82.68%
Caco-2	-	0.5270	52.70%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6112	61.12%
OATP2B1 inhibitior	-	0.8495	84.95%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9558	95.58%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8023	80.23%
P-glycoprotein inhibitior	-	0.9370	93.70%
P-glycoprotein substrate	-	0.7066	70.66%
CYP3A4 substrate	+	0.5667	56.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8426	84.26%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9031	90.31%
CYP2C19 inhibition	-	0.9066	90.66%
CYP2D6 inhibition	-	0.9679	96.79%
CYP1A2 inhibition	-	0.8164	81.64%
CYP2C8 inhibition	-	0.9109	91.09%
CYP inhibitory promiscuity	-	0.9929	99.29%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6684	66.84%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.8725	87.25%
Skin irritation	-	0.6328	63.28%
Skin corrosion	-	0.9306	93.06%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5766	57.66%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8930	89.30%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6816	68.16%
Acute Oral Toxicity (c)	III	0.3843	38.43%
Estrogen receptor binding	-	0.5347	53.47%
Androgen receptor binding	+	0.6596	65.96%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.4803	48.03%
Aromatase binding	+	0.5934	59.34%
PPAR gamma	-	0.7761	77.61%
Honey bee toxicity	-	0.8208	82.08%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9470	94.70%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137262	O60341	LSD1/CoREST complex	90.41%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.94%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.76%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.71%	91.11%
CHEMBL2581	P07339	Cathepsin D	88.08%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.92%	96.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.44%	82.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.30%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.00%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.79%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.76%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	83.80%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.39%	86.33%

Plants that contains it

• Illicium dunnianum
• Illicium floridanum

Cross-Links

• PubChem: 14807806
• LOTUS: LTS0201047
• wikiData: Q105182589